Enantioselective synthesis of (S)- and (R)-alfa-methylserines: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-alfa-methylserinals
- Avenoza, A. 1
- Cativiela, C. 2
- Corzana, F. 1
- Peregrina, J.M. 1
- Sucunza, D. 1
- Zurbano, M.M. 1
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1
Universidad de La Rioja
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2
Instituto de Nanociencia y Materiales de Aragón
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ISSN: 0957-4166
Año de publicación: 2001
Volumen: 12
Número: 6
Páginas: 949-957
Tipo: Artículo
beta Ver similares en nube de resultadosOtras publicaciones en: Tetrahedron: Asymmetry
Resumen
This report describes the synthesis of enantiomerically pure (S)- and (R)-α-methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary α-amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinal building blocks. © 2001 Elsevier Science Ltd.